2-Oxazolidinone → HCID 53245829, compound

HRID 1805390Notes

Reaction equation

HRID 1805390 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C[O:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14](I)[CH:13]=[C:12](Br)[CH:11]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@@:26]2([CH3:38])[C@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:37])[CH2:27]2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C@:26]2([CH3:38])[C@@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([C:12]4[CH:11]=[C:10]([CH:15]=[C:14]([N:3]5[CH2:4][CH2:5][O:1][C:2]5=[O:6])[CH:13]=4)[C:9]([OH:8])=[O:18])[C:29]3=[O:37])[CH2:27]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 739492-OxazolidinoneHCID 21942573Methyl 3-bromo-5-iodobenzoateHCID 67234195HCID 67234195, compound

Product 1

HCID 53245829HCID 53245829, compound

Procedure

The title compound was prepared in analogy to Example 95 starting from oxazolidin-2-one (commercially available), 3-bromo-5-iodobenzoic acid methylester prepared in Example 92, (1R,2R) and (1S,2S)-2-(4-chlorophenyl)-2-methylspiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 2. LC/MS m/e calcd. for C27H21ClN2O5: 488, observed (M+H)+: 489.1 1H NMR (400 MHz, DMSO-d6) δppm 1.66 (s, 3 H) 2.18 (d, J=4.80 Hz, 1 H) 2.38 (d, J=5.05 Hz, 1 H) 4.12 (t, J=8.08 Hz, 2 H) 4.47 (t, J=7.96 Hz, 2 H) 6.95 (d, J=8.08 Hz, 1 H) 7.15 (t, J=7.45 Hz, 1 H) 7.25-7.34 (m, 5 H) 7.45 (d, J=7.33 Hz, 1 H) 7.59-7.62 (m, 1 H) 7.85 (t, J=2.02 Hz, 1 H) 8.12 (s, 1 H).

Sources & evidence

ORD record
ord-7fa1540aa7be407b8f5c7a44103449dc
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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